Winston is a boy at Vicky's highschool that she has a crush on. She keeps his hair and gum in her diary, and attempts to become a cheerleader just to impress him. Despite doing seemingly everything she needed to win him over, he still rejected her because she did not manage to become a cheerleader.
Winston is fashioned after the most offensive stereotype for a British person possible: A snobby, nerdy boy with a posh accent, bad teeth, and a penchant for tea and "the hunt". Despite his geeky appearance, he is very popular amongst the ladies.
He enjoys flirting, drinking tea, and referring to "the hunt". He is very shallow and only dates girls who strickly conform to his likes. His fascination and love for the hunt gives him many likes, including a love for manly men's flatulence (such as Jorgen's) and women with body hair. He is terrified of the color pink, as well as squirrels.
When Timmy read Vicky's diary, he found that she had a secret crush on Winston Dunnsworth, a British boy at Dimmsdale High School. Winston did not return the affection, so Vicky was trying various ways to win him over. Timmy attempted to sabotage Vicky's advances, but every time he did something intended to gross Winston out, he liked it(because what they did reminded him of the hunt). To win him over, Vicky rehearsed at cheerleader tryouts, but because of Wanda and Timmy's interference, she blurted out her horrible secrets in her cheers, causing Dunnsworth to become offended. Vicky broke down and started crying.
Elsewhere, Timmy's parents hired Evil Babysitters that were even worse than Vicky when she didn't show up for work, so Timmy set out to make her happy again by having her rescue Winston from his worst fear: pink squirrels. Timmy returned to Vicky the next day, still at her highschool crying in the same spot she had been before, and accidentally revealed that he had been peeking in Vicky's diary when he told her the "fat pink squirrel she hated" (Wanda) was attacking Dunnsworth. Vicky used a truth serum to get Timmy to confess he had been reading her diary, and then used Timmy to beat away Wanda, leaving them both stuck in the ground head first. Vicky then left hand and hand with Winston, and it appeared they were together, when he suddenly dumped her because she wasn't a cheerleader, and then he flew away with an umbrella. Vicky cried again, but went back to babysitting Timmy.
- He is possibly a parody of Austin Powers.
- When he flies away with the umbrella, it's a reference to Mary Poppins.
- Winston is the name of Jorgen Von Strangle 's former godchild.
- He shares the same first name as Former British Prime Minister Winston Churchill.